7-CHLORO-2-IODOTHIENO[3,2-B]PYRIDINE-6-CARBONITRILE synthesis

4synthesis methods

Product Name:7-CHLORO-2-IODOTHIENO[3,2-B]PYRIDINE-6-CARBONITRILE
CAS Number:700844-17-3
Molecular formula:C8H2ClIN2S
Molecular Weight:320.54

700844-09-3 Synthesis

7-CHLOROTHIENO[3,2-B]PYRIDINE-6-CARBONITRILE

700844-09-3
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7-CHLORO-2-IODOTHIENO[3,2-B]PYRIDINE-6-CARBONITRILE

700844-17-3
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Yield:-

Reaction Conditions:

Stage #1: 7-chlorothieno[3,2-b]pyridine-6-carbonitrilewith lithium diisopropyl amide in tetrahydrofuran;n-heptane;ethylbenzene at -78; for 0.333333 h;
Stage #2: with iodine at -78; for 5.2 h;

Steps:

9 Reference Example 9 7-CHLORO-2-IODOTHIENO [3,2-b] pyridine-6-carbonitrile

Reference Example 9 7-CHLORO-2-IODOTHIENO [3,2-b] pyridine-6-carbonitrile To a solution of 7-CHLOROTHIENO [3,2-b] pyridine-6-carbonitrile (735 mg, 3.78 MMOL) in 20 mL of tetrahydrofuran AT-78°C is added dropwise 2.0 M lithium diisopropylamide in heptane/tetrahydrofuran/ethylbenzene (2.2 mL, 4.40 MMOL). After stirring for 20 minutes, a solution of iodine (1.15 g, 4.53 MMOL) in 4 mL of tetrahydrofuran is added dropwise over 20 minutes. The reaction mixture is stirred at - 78°C for 5 hours, then 20 mL of chloroform and 10 mL of water are added. The mixture is stirred at room temperature overnight, then partitioned between water and chloroform. The organic layer is washed with a solution of sodium thiosulfate, followed by water, then dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash column chromatography eluting with 5% methanol in DICHLOROMETHANE to provide 750 mg of 6-CHLORO-2-IODOTHIENO [3,2- b] pyridine-7-carbonitrile as yellow crystals, mp 209-211 °C ; 1 H NMR (DMSO-d6) 88. 17 (s, 1H), 9.05 (s, 1H). Analysis for C8H2CIIN2S : Calcd : C, 29.98 ; H, 0.63 ; N, 8.74 Found: C, 29.61 ; H, 0.87 ; N, 8.68.

References:

WO2004/48386,2004,A2 Location in patent:Page 80